ATE417043T1 - METHOD FOR PRODUCING IMIQUIMOD AND ITS INTERMEDIATE COMPOUNDS - Google Patents
METHOD FOR PRODUCING IMIQUIMOD AND ITS INTERMEDIATE COMPOUNDSInfo
- Publication number
- ATE417043T1 ATE417043T1 AT05012621T AT05012621T ATE417043T1 AT E417043 T1 ATE417043 T1 AT E417043T1 AT 05012621 T AT05012621 T AT 05012621T AT 05012621 T AT05012621 T AT 05012621T AT E417043 T1 ATE417043 T1 AT E417043T1
- Authority
- AT
- Austria
- Prior art keywords
- aryl
- alkyl
- group
- imiquimod
- producing
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 2
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical class C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 title abstract 2
- 229960002751 imiquimod Drugs 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 abstract 3
- -1 hydroxylamino Chemical group 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 150000002429 hydrazines Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A process for the preparation of Imiquimod and novel hydroxylamino and hydrazine derivatives, useful as intermediates in its preparation. <??>The process comprises the reaction of 4-chloro-1-isobutyl-1H-imidazoÄ4,5-cÜquinoline, of formula (I) <CHEM> with a compound of formula (II) NH2-X (II) wherein X is an -OR or -NR1R2 group, in which R is hydrogen, a C1-C6 alkyl, aryl-C1-C4 alkyl, aryl or -SO3H (sulfonic) group; and each of R1 and R2 is independently hydrogen, a C1-C6 alkyl, aryl-C1-C4 alkyl, aryl or -SO2R3 group, in which R3 is an aryl group and, if necessary, the reaction with a reducing agent.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT001282A ITMI20041282A1 (en) | 2004-06-24 | 2004-06-24 | IMIQUIMOD PREPARATION PROCEDURE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE417043T1 true ATE417043T1 (en) | 2008-12-15 |
Family
ID=34937394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT05012621T ATE417043T1 (en) | 2004-06-24 | 2005-06-13 | METHOD FOR PRODUCING IMIQUIMOD AND ITS INTERMEDIATE COMPOUNDS |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20060004202A1 (en) |
| EP (1) | EP1609792B1 (en) |
| JP (1) | JP2006008686A (en) |
| AT (1) | ATE417043T1 (en) |
| CA (1) | CA2510576A1 (en) |
| DE (1) | DE602005011530D1 (en) |
| ES (1) | ES2317104T3 (en) |
| IT (1) | ITMI20041282A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20051292A1 (en) * | 2005-07-08 | 2007-01-09 | Dipharma Spa | PROCEDURE FOR PURIFICATION OF IMIQUIMOD |
| US7943771B2 (en) * | 2007-01-24 | 2011-05-17 | Chemagis Ltd. | Imiquimod production process |
| US7659398B2 (en) | 2007-02-14 | 2010-02-09 | Chemagis Ltd. | Imiquimod production process |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL73534A (en) * | 1983-11-18 | 1990-12-23 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinoline-4-amines,their preparation and pharmaceutical compositions containing certain such compounds |
| US4929624A (en) * | 1989-03-23 | 1990-05-29 | Minnesota Mining And Manufacturing Company | Olefinic 1H-imidazo(4,5-c)quinolin-4-amines |
| US5175296A (en) * | 1991-03-01 | 1992-12-29 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-c]quinolin-4-amines and processes for their preparation |
| US5741908A (en) * | 1996-06-21 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Process for reparing imidazoquinolinamines |
-
2004
- 2004-06-24 IT IT001282A patent/ITMI20041282A1/en unknown
-
2005
- 2005-06-13 AT AT05012621T patent/ATE417043T1/en not_active IP Right Cessation
- 2005-06-13 ES ES05012621T patent/ES2317104T3/en not_active Expired - Lifetime
- 2005-06-13 EP EP05012621A patent/EP1609792B1/en not_active Expired - Lifetime
- 2005-06-13 DE DE602005011530T patent/DE602005011530D1/en not_active Expired - Fee Related
- 2005-06-23 JP JP2005182864A patent/JP2006008686A/en active Pending
- 2005-06-23 CA CA002510576A patent/CA2510576A1/en not_active Abandoned
- 2005-06-23 US US11/159,129 patent/US20060004202A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1609792A1 (en) | 2005-12-28 |
| ES2317104T3 (en) | 2009-04-16 |
| DE602005011530D1 (en) | 2009-01-22 |
| EP1609792B1 (en) | 2008-12-10 |
| CA2510576A1 (en) | 2005-12-24 |
| ITMI20041282A1 (en) | 2004-09-24 |
| JP2006008686A (en) | 2006-01-12 |
| US20060004202A1 (en) | 2006-01-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RER | Ceased as to paragraph 5 lit. 3 law introducing patent treaties |